


Midnight Whiskey

by imamotherfuckingstarlord



Category: Star Trek: Alternate Original Series (Movies)
Genre: Anal, Double Penetration, Enterprise, F/M, James T Kirk - Freeform, Jim x Reader, Leonard McCoy - Freeform, Multi, Oral, Star Trek - Freeform, Threesome, bones - Freeform, jim x reader x leonard, leonard x reader, star trek aos - Freeform, star trek smut
Language: English
Status: Completed
Published: 2016-10-10
Updated: 2016-10-10
Packaged: 2018-08-20 13:02:25
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,485
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8250046
Author URL: https://archiveofourown.org/users/imamotherfuckingstarlord/pseuds/imamotherfuckingstarlord
Summary: A night of drinking while on leave, turns into something very fun on the Enterprise with the Captain and Doctor.





	

Your steady gaze flits back and forth between the two handsome men sitting across from you. One with the perfect shade of blond hair, accompanied by bright blue eyes that were constantly peering right into yours. The other man, a little older, but nonetheless handsome. His brooding face and brown hair that was begging for your fingers to run through it, made you ache between your legs. Your skin flushes red with your thoughts, as you quickly take down the rest of the beer in front of you. Both men had caught your eye as soon as you stepped onto the Enterprise a year ago, it was a constant flirtation between the men and you. And tonight, the copious amounts of alcohol in your system had given you quite the nerve.

“Hey, I have an idea,” you casually announce, pushing the empty beer bottle in front of you.

Jim cocks his eyebrow with a smirk, “Oh, do you?”

Biting your lip, you looked over to Leonard, “I mean, if you two old grumps can’t handle-”

Bones immediately cuts you off with a loud scoff, “Listen darlin’, I’m not that old, but the night sure is young.” And with the doctor’s words, Jim offers to pay the bar tab as Leonard throws an arm around your shoulder.

This sudden act of affection catches you off guard, “Whoa, Bones. Feeling a little touchy feely tonight?” You tease, letting your hand slip around his waist, his leather jacket felt cool under your skin. He just smiles leading the two of you outside the bar and onto the street, your head spins in a haze of beer and Leonard’s touch.

“Hey! Can’t leave without the party,” Jim shuffles behind the two of you, his eyes taking in the sight of Bones and you, “Oh, don’t you two look cute.”

“Dammit Jim, if I’m not mistaken, is that a hint of jealously I hear?” Leonard’s southern drawl deepens, as he smirked widely, his grip around your shoulder tightening.

“Nah, Bones. Y/N knows exactly what she’s missing,” Jim hinted with such a look of pure glee on his face that Bones halts in his steps, peering at the blond man then you, his eyebrows rise up in question.

“It was one time! Jim was all mopey about his birthday, it was one kiss!” You protest, pulling away from Bones, “You two are a pain in my ass.”

You start walking ahead, trying to conceal the smile on your face. The Captain and Doctor linger behind for a brief moment, before appearing on at your side. Jim throws his arm around you, pulling you into his side.

“Be nice, Jim,” you warn with a grin, “Or I won’t share the whiskey I have in my room.”

Leonard laughs as Jim places a chaste kiss on your forehead, “Oh, I’ll be very nice beautiful.”

You laugh nervously, knowing Jim well enough to realize that was a promise.

“Alright, let’s go drink some damn whiskey,” Bones exclaims, encouraging Jim and you to hurry up as he walks ahead.

Fifteen minutes later, the three of you stumble on to the Enterprise, laughing at Jim’s feeble attempt to sing a certain classic song. You lead the two men to your quarters, stopping at the door and turning to face them.

“Okay, there is only one rule. Don’t touch anything.” The men laugh as you lead them into your quarters, you immediately head to the small counter at the far end of the room. Jim hardly notices the pile of clothes on the floor next to your bed or the stacks of books on the table. It’s Leonard’s eyes that widen at the sight of your quarter, he knew you were busy down in engineering with Scotty, but still.

“Darlin’, not to be rude,” Bones starts to say looking away from the various papers strewn around the room, as you take out a couple of glasses, “But you are a slob. I thought Jim was bad, but-”

Jim tries to stifle his laugh as you glare at the Doctor, whiskey bottle in hand, “Leonard McCoy, where are your southern manners? No whiskey for you.”

“Ah, come on Y/N. He can’t help himself, Mr. Sensitive remember?” Jim offers, his lips smile as they touch the rim of glass you poured for him.

“Right, I forgot. Leonard has the perfect bedside manners.” You muse, holding out your glass toward Jim, who clinks his against yours.

“Dammit, stop talking like I’m not here.” Bones grumbles, reaching for a glass of whiskey. You apologize with a smile, letting the whiskey run smoothly down your throat.

“Sweet, Jesus.” Leonard groans, “This is perfection.”

“I traded it will Chekov.”

“What did you trade for?” Jim inquires with curiosity, taking another sip from his drink.

“Sexual favors,” you deadpan. The two men choke on their drinks, eyes widen as they both stare at you speechless. The expressions on their faces have you bursting out in laughter that fills the entire room, “I’m kidding, guys!”

Their faces relax, as your laughter comes to a slow stop, “No, I gave him slow dancing lessons.”

Jim’s blue eyes lit up, but you immediately cut him off, “Don’t you dare give that sweet boy a hard time!”

“I was just going to suggest some music,” Jim smirks, looking around the room.

“Music could be nice,” Leonard adds setting down the empty glass of whiskey. You shrug, letting Jim know he could pick anything he wanted, because you had hooked up the system in your quarters to play music. You watch Jim happily going over the songs in your library on the PADD, until he touches one and a familiar song fills the room.

“Oh, that’s a good one.” You start to sway your head to the music, until Jim reaches out his hand toward you.

“Really?” You question and Jim just nods, waiting for you to take his hand. You look over to Leonard, who leans against the counter with a smile. You let Jim lead you to the center of the room, sliding your hands around his neck as his hands come down to your waist.

“I haven’t slow danced since high school.” He admits trying to follow your steps, but his feet had other ideas. You try not to laugh as he painfully kept stepping on your toes.

The two of you dance for only a minute longer before Leonard pulls Jim from you, “Dammit Jim, move aside. She deserves a decent dancing partner.”

Jim just laughs as he holds up his hands in defeat, walking back to the counter to refill his glass with whiskey. He watches your body leaning into Bones, the two of you dance as if it was something you did every nsight. Leonard had his hands on your waist, the warmth of his skin burned right through your dress. You could feel his fingers gripping at you, a hint of desperation pulls inside you. Your chest heaves slowly as Leonard’s eyes look into yours, something fills the air that you can’t quite pinpoint, but it has you soaking through your panties. And that’s when you feel Jim behind you, his breath steady on your neck. You feel no need to hesitate to lean against his chest, trusting the reassurance in Leonard’s eyes as his hands move up from your waist and up your side. His steady hands slide up to your face, grazing his thumb against your cheek. Jim’s hands rest at your waist, his lips press a kiss on your earlobe, sending a chill down your spine that weakens your knees.

“Darlin’, I’ve wanted to do this for a long time,” Leonard whispers as he leans forward to press his lips against yours. The moment your lips touch, a moan releases from your throat, pulling him closer by the waist and slamming him into you. Leonard groans into your mouth, pulling away suddenly and flipping you around, so you were against his chest. You are met with two bright blue eyes, that were staring right at your lips, that were red and a bit swollen. Reaching out to Jim, who fills in the gap between the two of you, he pushes you against Leonard, giving you a feel of the doctor’s cock that was hard underneath his pants. Your instant reaction to grind your bottom against Leonard, who moans into your ear. Jim’s hand moves to the hem of your skirt, as he places a soft kiss on your lips. The taste of whiskey on his tongue as you tug lightly on his shirt, moving the Captain closer to you. It’s then you realize the position you were in, right in between the best looking fellas on the Enterprise, and boy did you feel lucky. Greedy as well, the thought of having them both the way you were positive no one else has had, fills you up with excitement. You head moves back against Leonard’s shoulder, he leans in and starts to kiss your pressure point, causing your body to arch in pleasure.

“I think she likes that, Bones.” Jim smirks, nodding to his friend.

“She sure does, Jim.” Leonard mumbles, his hands sliding up from your waist and slowly cupping your breasts, massaging them gently. You are too distracted with Bones’ strong hands pawing over you, that you do not notice Jim moving down to his knees until his fingers graze your thigh. You gasp into Leonard’s mouth, pulling away and looking down. Jim smirks up at you before leaning forward and placing a kiss on your thigh. His fingers slide up under your dress, softly palming your soaking pussy.

“She’s nice and wet, Bones.” Jim reports, his head disappearing under the dress. Your senses roar in every direction of your body as Jim continues to kiss your inner thighs, slowly parting your legs.

Leonard moves your dress up by the waist; exposing your lower half to the Captain. Bones slides his hands up against your skin, his palms move across your stomach, “You feel so good,” he gruffly murmurs into your ear in a tone that you hadn’t heard from him. A tone that could very well send you over the edge, as Jim pulls down your black panties letting them slide down to your ankles. The Captain quickly helps you take off your flats, removing the panties and tossing them aside. He leans back for a moment, drinking in the sight of your pulsing pussy.

“Please, Jim. Touch me,” you whimper underneath Leonard’s touch, his hands had made their way to your breast, pulling down on your bra. His fingers pinch at your hardened nipples, having you panting against his chest. You look up at Leonard, his eyes filled with lust as you bring his head closer to yours. His lips attack hungrily, tongue pressing against your lips opening them up for him to enter. You slink your hand around his neck, moaning into his mouth, biting down on his tongue. His cock presses hard against your back, but before you could react to it, Jim’s tongue is lapping at your pussy.

“Jim!” You murmur pulling from Leonard’s lips, gasping for air. Your hand moves down toward Jim, running your fingers through his hair. His tongue pushes past your folds, hitting the sweet spot quickly and you know then how experience the Captain really was. Your breaths are sharp as Jim burrows deeper into your pussy, his hands grip at your waist, pulling you closer into his mouth. With Leonard working on your nipples and Jim reaching far into you, it’s all too much as you buckle under Jim’s mouth. He moans as you convulse against his lips, your taste is sweet and intoxicating as he licks once more before pulling away. Jim stands up, looking flush and amused, nodding to his friend, who pulls up your dress over your head.

“Well darlin’, I think it’s time to take this to the bed.” Leonard whispers in your ear, unhooking your bra and pulling down the straps.

“Why am I the only one naked?” You tease, turning to face the Doctor, pressing your body against his. His clothed cock sprang against you, his hands work down to your bottom, grabbing a handful before giving it a light smack. You grin with excitement and the slight sting on your rear, as you pull Leonard’s shirt over his head. You secretly condemn Starfleet for making uniforms that hid away the Doctor’s outstanding physique, running your hands down his broad chest. He smirks down at you, his hands lifting your breasts up, thumbs rubbing your nipples. You reach behind you, motioning for Jim to join. It’s a moment before you feel his bare chest against your back, his lips kissing the edge of your shoulders. You turn to face him, immediately biting down on your lip drinking in the sight of the shirtless Captain. Making a mental note to write a letter of recommendation to Starfleet to change up the uniform, you were thinking definitely shirtless for the men, at least for these two.

“I think it’s time for me to give a little back,” you smirk reaching for Jim’s belt buckle and undoing it. He doesn’t take his eyes off you as your fingers make quick work at unzipping his pants and pulling them down. His white boxers do nothing to conceal his hard cock, begging to be released. Jim moans softly as you palm his cock with one hand, before pulling down his boxers.

“You too, Lee.” You look over your shoulder, eyeing the doctor’s slacks. Turning back to Jim, you hear Bones shuffling behind you, no doubt removing his pants and boxers. You take Jim’s hand and lead him to your bed, pushing him down. Jim moves up on the bed, resting against a pillow pumping his cock as you crawl over to him. Licking your lips, you maintain eye contact as your mouth comes down around his very endowed cock. He jerks underneath you, making you move further down his cock. Your jaw aching a little, but the pre cum taste is addictive, so you keep going. The bed’s weight shifts as Bones comes up from behind you, his warm hands rest on your hips.

Your lips glide up Jim’s cock, pulling away for a moment and looking over your shoulder, “Leonard, please.”

“Please, what sweetheart?” He smirks, the pleading in your voice turning him on even more.

“Fuck me, Doctor.” You beg, smiling at Jim as he grips his cock, waiting for your lips. Not waiting for Leonard’s response, you quickly go back to deep throating the Captain’s cock. Your mouth rides up and down, your moans against his cock vibrate Jim closer to release.

“Y/N, keep going beautiful.” Jim whispers out in a moan, his hands caressing your hair, gently pushing you down further. You work faster, but falter for a moment when you feel Leonard moving closer behind you. You could feel his cock edging at the opening of your pussy, one of his hands on your back. Pushing back, eager to have him fill you up, the doctor chuckles, “Patience, darlin’.”

And you knew then, he was not going to give in easily, so you slowed down your movements on Jim’s cock wanting to make it all last longer.

Leonard adjusted himself comfortably, proceeding with his teasing until you groan loudly around Jim’s cock.

“Bones, stop teasing her,” Jim chuckles, pushing away the hair from your face, “Give her what she wants.”

Leonard mumbles under his breath, something about, “The teasing is the best part,” before painstakingly pushing himself into you. You gasp at the sudden fullness, holding still for a moment before pushing down on Leonard’s cock, signaling for the man to get to work. Leonard doesn’t have to be told twice, his hands grip your waist, pulling against his dick.

With Jim fully in your mouth, you can barely get a moan out, so instead you grip at the sheets underneath you.

“Jesus, sweetheart. You’re so nice and tight.” Leonard leans forward, his weight is felt on your back. His large hands reach underneath for your breast, cupping them tightly as he continually pounds into you. You move with the rhythm Bones sets, moving up and down Jim’s throbbing cock. The moans coming from the each of you fill the room and if there was another soul on the Enterprise, they could surely hear it.

“I’m going to-” Jim squirms underneath you, his hips jerking up. You can almost taste his cum, so you move quickly moaning against him as Bones picks up speed. Lee’s cock twitches inside you, pushing further and further until you don’t think you can hold on longer. Jim comes firsts, his body convulsing as you take everything he has to give. His taste was surprisingly sweet, as you lick his tip before resting your head on his hip bone. Jim reaches for your hand, holding it softly as you moan against his skin.

“Oh, god. Lee! I’m going to come!” Leonard’s chest was against your back, his hips thrusting against you, the sound of flesh hitting flesh takes you over the top.

“Sweetheart, come on my cock,” Lee’s southern accent comes out thick and rough. His encouraging words set you off, you moan out his name as you jerk against him. The warmth from your orgasm surrounds Leonard’s cock, as he gives you three final thrusts before his arm pulls you closer to him. His cock jerks inside you for a minute as the two of you catch your breath. Leonard lowers you down on to Jim, placing a kiss on the small of your back before settling on the edge of the bed.

Your pussy feels sensitive, but you want more. You kiss Jim’s hip bone, causing the blond man to smile at you. His hands reach down to pull up to him, you laugh as his lips press against yours. His tongue pushes between your lips, his arms tighten around your waist. The feel of Jim’s cock against your stomach has you wet again.

Your head moves down to his neck, trailing kisses up to his earlobe and lightly tugging it with your teeth.

“Fuck me, Jim.” You murmur into his ear. The Captain gives his famous smirk, his hands moving your hips up.

“I plan to, beautiful,” Jim adjust himself so his cock was lined up with your pussy. You look over your shoulder at Leonard, who had gotten off the bed and was pouring himself a glass of whiskey. He smiles at you as he raises the glass to his mouth, you look down at Jim, the feeling of desire blankets over you. You take his cock in your hand, pumping it a few times getting it harder. Jim lifts your hips up and then slowly pulls you down onto his cock. At the same time, both of you moan out loud, the feeling of sensitivity vanishes and is replaced with pleasure.

“Fuck, Jim!” You whimper, rocking your hips back and forth, cowgirl style. Jim’s hands paw at your breast, massaging them roughly as he brings his knees up behind you. Your hands move back onto his knees, back arched, breast bouncing as you slam down on his cock.

“Shit, beautiful,” Jim smiles, reaching for your neck and pulling you all the way down for a kiss. His plump lips slowly move against yours, his fingers clutched around your neck. He kisses you deeper, more passionate as he thrust his hips up. You push off him, resuming your position against his knees.

You look over to where Bones stood, “Are you going to just stand there or join, Dr. McCoy? Oh and bring that whiskey.”

Leonard grinned, chugging down the rest of his drink and making his way to the bed with the bottle in hand. His cock sprung to life as he drew closer to you. Reaching your hand out to him for the bottle, he hands it over with a smile. Bones gets onto the bed, moving right next to you. His eyes watch you dip your head back and letting the whiskey flow down your throat, some spilling out the corner of your mouth. Leonard grabs your face in his hands, leaning his head forward he kisses you roughly, sucking the whiskey from your lips.

“Come closer, Lee,” you command, setting the bottle of whiskey to your side, “Want some whiskey, Captain?” 

Jim grins, raising his head so you can pour some of the alcohol into his mouth. You lean over to place the bottle on the night stand and kiss Jim on the lips. Starting your speed up again, Jim moans out loud, his fingers squeeze your thighs. You reach out to Leonard’s cock, jerking your hand up and down his large dick. His mouth moves to your shoulder, biting down on it with a loud groan as you move your hand faster. It takes you a moment to get a good rhythm going between the two men, but once you get the hang of it, the pleasure becomes overwhelming. But you aren’t ready to come again, so you abruptly stop all movement. The two men look at you in confusion as you get off Jim.

“What’s going on, darlin’?” Bones inquires.

“I want both of you, at the same time.” You motion for Jim to get up and Bones to trade places with him. The two men do as you say, both eager to feel you riding their cocks.

Leonard settles on his back, anticipation fills the air as you lay on top of him, your back pressed to his chest. He immediately reaches for your breast, cupping them gently, your nipples harden under his fingertips.

“Jim, come here.” You reach out for the blond man, who doesn’t hesitate to come to you, “I want both of you. Please, now.”

Jim’s eyes linger to Leonard, who nods at him. Bones pushes your hair from his face, “Alright, darlin’. I’m going to enter you nice and slow.”

Nodding, you brace yourself for the brief pain that will come, knowing the pleasure would soon follow. Jim caresses your thighs gently, “Relax, beautiful,” his blue eyes smile down at you. Unlike before, there is no teasing from the doctor, just gentleness as his cock slowly enters you from behind. The filling is foreign for a moment as he fills you up, being careful to not move.

He groans underneath you, “Jesus, sweetheart. You are so damn tight. One move and I’m a done man,” Leonard buries his mouth into your neck. You clench your ass cheeks together, teasing the doctor, who moans loudly.

“Alright, Jim. I’m ready for you.” You wave the handsome blond closer.

Bones holds himself in place and waits for the captain to enter you. Jim grabs your legs, pulls them up against his chest and strokes himself, hardening in his own hands before he enters you. “Lee, Jim, fuck me. Fuck me hard!” Your voice was trembling as both men fill your request. The sensation was disorienting as pleasure came from both men. You couldn’t even tell who was who. Their cocks move deep inside of you and hit all the right spots. Jim could feel your walls clench around his cock and Bones couldn’t believe how nice and tight you were.

The three of you move in unison as your loud moans fill the room, your head spinning as if you were drunk. Your entire body throbbing with pleasure as you shout out their names, as both men thrust into you. The room’s air fills with the scent of sex and the sound of flesh hitting flesh.

Leonard grunts underneath you, “Fuck, darlin’. I could do this all day.”

“Stop trying to show off Bones,” Jim murmurs as he pounds into your pussy, his fingers tightly grip around your ankles.

“Shut up, Jim.” Leonard grumbles, sliding his hand down your stomach and over your clit.

Nearly breathless, you can hardly speak as the two men drive their cocks into you, but you manage a, “Will you two shut up and fuck me!” before moans take over your words. And then the room falls silent, only the moans coming from the three of you. The two men focus on making you come, as they move faster and faster, until you aren’t sure your body could handle anymore. As the three of you edge closer to release, the movements of your bodies grew eager; the buildup was almost too much.

Then it happens; a simultaneous explosion of gratified pleasure. Jim and Bones both thrust into you one last time and cause you to wither between them. The three of you stay still and let your bodies rest in an entanglement of limbs.

Jim finally kisses your legs before he removes them from his shoulders. Leonard’s’ chest was heaving heavily underneath you and you let yourself slide off of him.

You pant as if you just ran a 5k marathon, leaning into Bones and placing a kiss on his lips. He moans softly, caressing your face with his thumb. Jim falls down next to you on the bed, his hair ruffled and cute. He pulls you into his side, kissing you on the forehead, resting his hand across your waist.

Bones gets off the bed and heads to the fridge, looking for water. He comes back with two cups of water, “After vigorous activity, the human body needs to stay hydrated.”

Jim and you laugh, as he hands a cup to you. Taking a healthy gulp, you hand it over to Jim, who finishes it off. Bones places his empty cup on the end table and collapses on the bed, his feet at your head.

“I don’t know about you two, but I’m exhausted.” The doctor mumbled into the sheets, you toss him a pillow so he could sleep comfortably. “Thank you, sweetheart.”

You move down on the bed, pulling the crumple up blanket over the three of you, resting your head on the soft pillow. Jim returns his arm around your waist, snuggling into your back. You feel Leonard’s hand on your calf, softly rubbing circles into your skin. The two men’s little gestures lull you to slumber, until Bones’ voice jerks your eyes open.

“One last thing,” his head peeks up from under the covers.

“What McCoy?” you groan into the pillow.

“Who gave you more orgasms?”

Jim snorts behind you, “Oh come on Bones. That’s not fair, Y/N knows how much more experience I am.”

The two men immediately break into a quiet bicker until you shout, “Enough. You two are completely ridiculous! I wasn’t counting. I guess we’ll have to do this again and keep score next time.”

You smile as the room falls silent with your words, neither men protesting but both falling asleep with grins on their faces


End file.
